Selective preparation of polycyclic aromatic hydrocarbons. Part 4.1 New synthetic route to anthracenes from diphenylmethanes using Friedel–Crafts intramolecular cyclization

Abstract

Preparation of several anthracenes from diphenylmethanes by direct Bradsher-type reaction, which incorporates formylation of a hydrocarbon followed by Friedel–Crafts intramolecular cyclization, is presented. The present method involving the action of Cl₂CHOMe and TiCl₄ on a variety of diphenylmethanes (constructed such that electrophilic substitution occurs ortho to the biphenyl linkage) offers a convenient, mild, one-pot synthesis of substituted anthracenes.

References

1. For Part 3 in the series, see T. Yamato, H. Inoue, M. Fukumoto and M. Tashiro, Org. Prep. Proced. Int., 1995, 27, 412.
2. L. R. C. Barclay, in Friedel–Crafts and Related Reactions, ed. G. A. Olah, Interscience, New York, 1964, vol. 2, ch. 22.
3. C. L. Jackson and J. F. White, J. Am. Chem. Soc., 1880, 2, 391.
4. L. F. Fieser, Org. React., 1942, 1, 129.
5. C. K. Bradsher, Chem. Rev., 1987, 87, 1277; J. Am. Chem. Soc., 1940, 62, 486; C. K. Bradsher and F. A. Vingiello, J. Am. Chem. Soc., 1949, 71, 1434; F. A. Vingiello and P. D. Henson, J. Org. Chem., 1965, 30, 2842; 1966, 31, 1357; 1965, 32, 3205; F. A. Vingiello and J. R. Thornton, J. Org. Chem., 1966, 31, 659; F. A. Vingiello and A. Borkovec, J. Am. Chem. Soc., 1956, 78, 3205; 1958, 80, 1714.
6. M. Ahmed, J. Ashby and O. Meth-Cohn, J. Chem. Soc., Chem. Commun., 1970, 1094; M. Ahmed and O. Meth-Cohn, J. Chem. Soc., Chem. Commun., 1971, 2104; M. Ahmed, J. Ashby, M. Ayad and O. Meth-Cohn, J. Chem. Soc., Perkin Trans. 1, 1973, 1099.
7. T. Yamato, M. Komine, N. Sakaue, T. Matsuda, Y. Nagano and M. Tashiro, J. Chem. Res. (S), 1993, 146.
8. A. Rieche, H. Gross and E. Hoft, Chem. Ber., 1960, 93, 88; G. N. Taylor and K. B. Wiberg, Org. Synth., 1967, 47, 47.
9. M. Tashiro and T. Yamato, J. Org. Chem., 1979, 44, 3037.
10. (a) M. Tashiro and T. Yamato, Synthesis, 1981, 435; (b) T. Yamato, J. Matsumoto, K. Tokuhisa, K. Tsuji, K. Suehiro and M. Tashiro, J. Chem. Soc., Perkin Trans. 1, 1992, 2675; (c) T. Yamato, A. Miyazawa and M. Tashiro, J. Chem. Soc., Perkin Trans. 1, 1993, 3127; (d) T. Yamato, Y. Saruwatari, L. K. Doamekpor, K. Hasegawa and M. Koike, Chem. Ber., 1993, 126, 2501.
11. T. Yamato, N. Sakaue, K. Suehiro and M. Tashiro, Org. Prep. Proced. Int., 1991, 23, 617.
12. M. Tashiro, T. Yamato, G. Fukata and Y. Fukuta, J. Org. Chem., 1981, 46, 2376; T. Yamato, H. Kamimura, K. Noda and M. Tashiro, J. Chem. Res., 1994, (S) 424; (M) 2401.
13. G. Baddeley and A. G. Pendleton, J. Chem. Soc., 1952, 807.
14. W. M. Schubert and H. K. Latourette, J. Am. Chem. Soc., 1952, 74, 1829; I. Agranat, Y. S. Shih and Y. Bentor, J. Am. Chem. Soc., 1974, 96, 1259; I. Agranat, Y. Bentor and Y. S. Shih, J. Am. Chem. Soc., 1977, 99, 7068.
15. G. A. Olah, K. Laali and A. K. Mehrotra, J. Org. Chem., 1983, 48, 3360.
16. G. A. Olah, P. S. Iyer and G. K. S. Prakash, Synthesis, 1986, 513; T. Yamato, J. Synth. Org. Chem. Jpn., 1995, 53, 487 and references therein.
17. G. A. Olah, G. K. S. Prakash, P. S. Iyer, M. Tashiro and T. Yamato, J. Org. Chem., 1987, 52, 1881; A. Miyazawa, T. Yamato and M. Tashiro, Chem. Express, 1990, 5, 381; T. Yamato, C. Hideshima, M. Tashiro, G. K. S. Prakash and G. A. Olah, J. Org. Chem., 1991, 56, 6248; A. Miyazawa, A. Tsuge, T. Yamato and M. Tashiro, J. Org. Chem., 1991, 56, 4312; A. Miyazawa, T. Yamato and M. Tashiro, J. Org. Chem., 1991, 56, 1334 See also ref. 10c.
18. S. Kajigaeshi, T. Kadowaki, A. Nishida and S. Fujisaki, Bull. Chem. Soc. Jpn., 1986, 59, 97.
19. K. Rülmann, Synthesis, 1971, 238.